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• • B—PERFORMING OPERATIONS; TRANSPORTING
  • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
  • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
  • B01J29/00—Catalysts comprising molecular sieves
  • B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
  • B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
  • B01J29/70—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups B01J29/08 - B01J29/65
  • B01J29/78—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups B01J29/08 - B01J29/65 containing arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
  • B01J29/7815—Zeolite Beta
• • B—PERFORMING OPERATIONS; TRANSPORTING
  • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
  • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
  • B01J29/00—Catalysts comprising molecular sieves
  • B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
  • B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
  • B01J29/70—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups B01J29/08 - B01J29/65
  • B01J29/72—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups B01J29/08 - B01J29/65 containing iron group metals, noble metals or copper
  • B01J29/7215—Zeolite Beta
• • B—PERFORMING OPERATIONS; TRANSPORTING
  • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
  • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
  • B01J29/00—Catalysts comprising molecular sieves
  • B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
  • B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
  • B01J29/70—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups B01J29/08 - B01J29/65
  • B01J29/72—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups B01J29/08 - B01J29/65 containing iron group metals, noble metals or copper
  • B01J29/76—Iron group metals or copper
  • B01J29/7615—Zeolite Beta
• • B—PERFORMING OPERATIONS; TRANSPORTING
  • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
  • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
  • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
  • B01J37/20—Sulfiding
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
  • C07C15/02—Monocyclic hydrocarbons
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C4/00—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms
  • C07C4/02—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms by cracking a single hydrocarbon or a mixture of individually defined hydrocarbons or a normally gaseous hydrocarbon fraction
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
  • C10G47/00—Cracking of hydrocarbon oils, in the presence of hydrogen or hydrogen- generating compounds, to obtain lower boiling fractions
  • C10G47/02—Cracking of hydrocarbon oils, in the presence of hydrogen or hydrogen- generating compounds, to obtain lower boiling fractions characterised by the catalyst used
  • C10G47/10—Cracking of hydrocarbon oils, in the presence of hydrogen or hydrogen- generating compounds, to obtain lower boiling fractions characterised by the catalyst used with catalysts deposited on a carrier
  • C10G47/12—Inorganic carriers
  • C10G47/16—Crystalline alumino-silicate carriers
  • C10G47/20—Crystalline alumino-silicate carriers the catalyst containing other metals or compounds thereof
• • B—PERFORMING OPERATIONS; TRANSPORTING
  • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
  • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
  • B01J2229/00—Aspects of molecular sieve catalysts not covered by B01J29/00
  • B01J2229/30—After treatment, characterised by the means used
  • B01J2229/42—Addition of matrix or binder particles
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C2529/00—Catalysts comprising molecular sieves
  • C07C2529/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites, pillared clays
  • C07C2529/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
  • C07C2529/70—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups C07C2529/08 - C07C2529/65
  • C07C2529/72—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups C07C2529/08 - C07C2529/65 containing iron group metals, noble metals or copper
  • C07C2529/74—Noble metals
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C2529/00—Catalysts comprising molecular sieves
  • C07C2529/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites, pillared clays
  • C07C2529/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
  • C07C2529/70—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups C07C2529/08 - C07C2529/65
  • C07C2529/72—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups C07C2529/08 - C07C2529/65 containing iron group metals, noble metals or copper
  • C07C2529/76—Iron group metals or copper
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C2529/00—Catalysts comprising molecular sieves
  • C07C2529/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites, pillared clays
  • C07C2529/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
  • C07C2529/70—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups C07C2529/08 - C07C2529/65
  • C07C2529/78—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups C07C2529/08 - C07C2529/65 containing arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
  • C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
  • C10G2300/10—Feedstock materials
  • C10G2300/1096—Aromatics or polyaromatics
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
  • C10G2400/00—Products obtained by processes covered by groups C10G9/00 - C10G69/14
  • C10G2400/30—Aromatics
• • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
  • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
  • Y02P20/00—Technologies relating to chemical industry
  • Y02P20/50—Improvements relating to the production of bulk chemicals
  • Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts

Definitions

• the present invention relates to a hydrocracking catalyst for preparing valuable light aromatic hydrocarbons from polycyclic aromatic hydrocarbons derived from oil.
• polycyclic aromatic hydrocarbons in particular, bicyclic aromatic hydrocarbons such as naphthalene and alkyl-substituted naphthalene, are the main constituents of inexpensive oils derived from oil.
• light aromatic hydrocarbons resulting from the hydrocracking of polycyclic aromatic hydrocarbons are generally known as C6 ⁇ C13 hydrocarbons including benzene and alkyl-substituted benzene.
• polycyclic aromatic hydrocarbons are converted into light aromatic hydrocarbons using hydrocracking via the following reaction route.
• a representative bicyclic aromatic hydrocarbon that is, naphthalene
• one of the two benzene rings of naphthalene is hydrogenated, so that naphthalene is converted to tetralin one ring of which is a benzene ring and the other ring of which is a naphthene ring.
• the naphthene ring of the tetralin thus converted is continuously hydrocracked, ultimately obtaining a light aromatic hydrocarbon in which an alkyl group is substituted on the one benzene ring.
• the present inventors have prepared valuable light aromatic hydrocarbons from polycyclic aromatic hydrocarbons derived from oil and furthermore have produced a hydrocracking catalyst enabling such preparation, and therefore the present invention has been devised in response to the need by the market for the above techniques.
• an object of the present invention is to provide a novel hydrocracking catalyst for preparing valuable light aromatic hydrocarbons from polycyclic aromatic hydrocarbons.
• the present invention provides a hydrocracking catalyst for preparing valuable light aromatic hydrocarbons from polycyclic aromatic hydrocarbons derived from oil, comprising (i) beta-zeolite; (ii) pseudoboehmite; and (iii) one or more metals selected from among metals of Groups VIII and VIB, optionally containing one or more cocatalyst components selected from the group consisting of tin (Sn), phosphorus (P), boron (B), silicon (Si), bismuth (Bi), and lead (Pb).
• a hydrocracking catalyst for preparing valuable light aromatic hydrocarbons from polycyclic aromatic hydrocarbons derived from oil, comprising (i) beta-zeolite; (ii) pseudoboehmite; and (iii) one or more metals selected from among metals of Groups VIII and VIB, optionally containing one or more cocatalyst components selected from the group consisting of tin (Sn), phosphorus (P), boron (B),
• catalyst components are selectively included, so that a maximum amount of BTX can be produced from LCO.
• the present invention pertains to a hydrocracking catalyst for preparing valuable light aromatic hydrocarbons from polycyclic aromatic hydrocarbons derived from oil.
• polycyclic aromatic hydrocarbons used as the feed are the main constituents of inexpensive oils, for example, LCO (Light Cycle Oil), derived from oil.
• LCO Light Cycle Oil
• bicyclic aromatic hydrocarbons such as naphthalene and alkyl-substituted naphthalene are mostly included but the present invention is not limited thereto. Any hydrocarbon including polycyclic aromatic materials that may be derived from oil may be used.
• valuable light aromatic hydrocarbons produced by hydrocracking polycyclic aromatic hydrocarbons are generally known as C6 ⁇ C13 hydrocarbons including benzene and alkyl-substituted benzene.
• valuable light aromatic hydrocarbons include mainly BTX (Benzene, Toluene, Xylene).
• naphthalene a representative bicyclic aromatic hydrocarbon, that is, naphthalene is illustratively described.
• hydrogen is added to naphthalene in the presence of a catalyst, one of two benzene rings that constitute the naphthalene is hydrogenated, so that the naphthalene is converted to tetralin one ring of which is a benzene ring and the other ring of which is a naphthene ring.
• the naphthene ring of the converted tetralin is continuously hydrocracked, resulting in a light aromatic hydrocarbon in which an alkyl group is substituted on one benzene ring.
• one or more among the benzene rings of a polycyclic aromatic hydrocarbon are saturated via hydrogenation and thereby the polycyclic aromatic hydrocarbon is converted to a hydrocarbon comprising one benzene ring and one or more naphthene rings, after which the naphthene rings are hydrocracked, thus obtaining a valuable light aromatic hydrocarbon.
• the reaction that produces BTX from naphthalene may cause a variety of side-reactions. Because products resulting from such side-reactions have no BTX, the side-reactions may malfunction to decrease the amount of BTX in the products. Hence, the side-reactions should be suppressed in order to maximize the BTX yield.
• the first is a thermodynamic equilibrium between tetralin and naphthalene.
• the conversion of naphthalene to tetralin is essential in order for BTX to be prepared from bicyclic aromatic materials such as naphthalene. This is because BTX is produced by hydrocracking tetralin.
• the equilibrium is known to be shifted toward tetralin in proportion to a decrease in temperature and an increase in pressure.
• tetralin converted from naphthalene may be re-converted to naphthalene depending on the reaction conditions.
• the process conditions should be changed in such a manner that the reaction temperature is lowered by as much possible and the reaction pressure is increased, or the converted tetralin should be rapidly hydrocracked to thus produce BTX, whereby the concentration of tetralin in the feed is lowered and the conversion of tetralin to naphthalene is thus reduced.
• the hydrocracking performance of the hydrocracking catalyst according to the present invention is high and thus the re-conversion to naphthalene may be minimized, thereby maximizing the production of BTX.
• the second is a conversion of tetralin to decalin in which one benzene ring of the tetralin is additionally hydrogenated and thus both of two rings are saturated.
• the decalin produced in the presence of hydrogen at high pressure may be converted to paraffin via additional hydrocracking. When such a side-reaction occurs to a great extent, the amount of BTX in the product may be decreased.
• the amount of naphthene or paraffin produced is larger than that of BTX.
• the hydrogenation activity of the hydrocracking catalyst should be appropriately controlled so that the hydrogenation reaction for producing tetralin from naphthalene is promoted and the hydrogenation reaction for producing decalin from tetralin is suppressed.
• the hydrogenation activity of the hydrocracking catalyst according to the present invention is properly controlled, the production of naphthene and paraffin may be minimized and the production of BTX may be maximized.
• the third is an additional hydrogenation of BTX resulting from hydrocracking of tetralin, undesirably converting the BTX to cyclohexane-like naphthene.
• the produced naphthene may be converted to paraffin via additional hydrocracking.
• This side-reaction may take place when the hydrogenation activity of the hydrocracking catalyst is very strong, as in the second side-reaction as above. That is, the hydrogenation activity of the hydrocracking catalyst according to the present invention is controlled such that the additional hydrogenation of the produced BTX is suppressed, thereby maximizing the production of BTX.
• the hydrocracking catalyst includes (i) beta-zeolite; (ii) pseudo-boehmite as a binder; and (iii) one or more metals selected from among metals of Groups VIII and VIB, optionally containing one or more cocatalyst components selected from the group consisting of tin (Sn), phosphorus (P), boron (B), silicon (Si), bismuth (Bi), and lead (Pb).
• the metal of Group VIII of the hydrocracking catalyst may be cobalt, and the metal of Group VIB may be molybdenum.
• the cobalt or molybdenum component may be provided in the form of a sulfide. This is considered to be because the sulfidation of a metal oxide having no hydrogenation activity may result in appropriate hydrogenation activity and high resistance to poisoning caused by sulfur and nitrogen compounds present in the feed.
• the cocatalyst component of the hydrocracking catalyst according to the present invention may be tin (Sn).
• tin (Sn) may interact with the active metal of the hydrocracking catalyst, namely, cobalt or molybdenum, thus controlling the hydrogenation activity of cobalt or molybdenum, thereby increasing the BTX yield.
• the total Si/Al atom ratio of beta-zeolite that constitutes the hydrocracking catalyst falls in the range of 5 ⁇ 200, thus providing the cracking function of the hydrocracking catalyst necessary for production of BTX, particularly favored being 10 ⁇ 150.
• beta-zeolite exists in the form of an extrudate mixed with pseudo-beohmite as the binder, and the amount of beta-zeolite in the extrudate may be 10 ⁇ 95 wt % based on the total weight of the catalyst in order to maintain the mechanical strength of a support and ensure the cracking function of the hydrocracking catalyst necessary for production of BTX, particularly favored being 30 ⁇ 90 wt %.
• the amount of cobalt or molybdenum may be 0.1 ⁇ 20 wt % based on the total weight of the catalyst in order to ensure the hydrogenation activity of the hydrocracking catalyst for maximally producing BTX, particularly favored being 1 ⁇ 10 wt %.
• the amount of tin (Sn) may be 0.01 ⁇ 10 wt % based on the total weight of the catalyst in order to modify the hydrogenation activity of the hydrocracking catalyst via interaction with cobalt or molybdenum, particularly favored being 0.5 ⁇ 5 wt %.
• the number of active sites of the catalyst may be decreased, undesirably deteriorating the hydrogenation performance, resulting in lowered BTX yield.
• cobalt or molybdenum when cobalt or molybdenum is the main catalyst and tin is the cocatalyst and these are added in amounts larger than the above upper limits, cobalt or molybdenum which is the active metal and tin may be sintered, so that the number of active sites is similar compared to when using a hydrocracking catalyst within the above ranges, thus exhibiting a similar BTX yield or blocking the pores of beta-zeolite by the sintered particles, undesirably deteriorating the hydrogenation performance.
• the cobalt precursor used was cobalt nitrate hexahydrate (hereinafter, CNH). (Cobalt may be provided as a variety of precursors and is not limited only to the above precursor.)
• the above catalyst was prepared in the following procedures.
• CNH was first dissolved in distilled water thus obtaining a CNH aqueous solution with which beta-zeolite was then impregnated, followed by performing drying at 150° C. for 2 hours and continuous calcination at 500° C. for 2 hours, thereby preparing a Co-BETA catalyst.
• This catalyst was prepared in the same manner as in Example 1, with the exception that ammonium heptamolybdate was used instead of CNH.
• Mo may be provided as a variety of precursors and is not limited only to the above precursor.
• This catalyst was prepared in the same manner as in Example 1, with the exception that hydrogen hexachloroplatinate was used instead of CNH.
• Pt may be provided as a variety of precursors and is not limited only to the above precursor.
• This catalyst was prepared in the same manner as in Example 1, with the exception that palladium nitrate hydrate was used instead of CNH.
• Pd may be provided as a variety of precursors and is not limited only to the above precursor.
• This catalyst was prepared in the same manner as in Example 1, with the exception that iron nitrate was used instead of CNH. (Fe may be provided as a variety of precursors and is not limited only to the above precursor.)
• the catalysts thus prepared were sulfide using the following method, and then used in hydrocracking reaction. The results are shown in Table 1 below.
• R-LGO including DMDS as a feed for sulfidation was allowed to flow at a rate of 0.08 cc/min under conditions of a pressure of 50 bar and hydrogen supply of 90 cc/min, and the catalyst was heated to 232° C. and maintained at 232° C. for 6 hours, after which the catalyst was heated to 320° C. and maintained at 320° C. for 6 hours, so that the catalyst was sulfided.
• reaction conditions including a pressure of 80 bar and hydrogen supply of 90 cc/min were set, and then the reaction temperature was increased to 410° C. Thereafter, tetralin as a feed was allowed to flow at a rate of 0.08 cc/min, so that hydrocracking was carried out. After the steady-state was achieved, the reaction product was recovered at intervals of 8 hours to analyze components in the product using GC-MSD.
• the performance of the catalysts was compared based on the conversion of tetralin as the feed, the amount of monocyclic aromatic hydrocarbon having no naphthene ring in the liquid product, and the amount of C6 ⁇ C8 aromatic hydrocarbon such as BTX in the liquid product.
• Tetralin conversion (%) (100 amount of tetralin in product)/100*100
• This catalyst was prepared in the same manner as in Example 1, with the exception that the amount of Co was 1 wt % based on the total weight of the catalyst.
• This catalyst was prepared in the same manner as in Example 1, with the exception that the amount of Co was 3 wt % based on the total weight of the catalyst.
• This catalyst was prepared in the same manner as in Example 1, with the exception that the amount of Co was 10 wt % based on the total weight of the catalyst.
• This catalyst was prepared in the same manner as in Example 1, with the exception that the amount of Co was 20 wt % based on the total weight of the catalyst.
• This catalyst was prepared in the same manner as in Example 1, with the exception that the amount of Co was 30 wt % based on the total weight of the catalyst.
• This catalyst was prepared in the same manner as in Example 1, with the exception that USY zeolite was used instead of beta-zeolite.
• This catalyst was prepared in the same manner as in Example 1, with the exception that amorphous SiO 2 —Al 2 O 3 was used instead of beta-zeolite.
• Co and Sn may be provided as a variety of precursors and are not limited only to the above precursors.
• This catalyst was prepared in the same manner as in Example 7, with the exception that ammonium heptamolybdate was used in lieu of CNH.
• This catalyst was prepared in the same manner as in Example 7, with the exception that chromium (III) nitrate was used in lieu of tin chloride. (Cr may be provided as a variety of precursors and is not limited only to the above precursor.)
• This catalyst was prepared in the same manner as in Example 7, with the exception that nickel nitrate was used in lieu of tin chloride. (Ni may be provided as a variety of precursors and is not limited only to the above precursor.)
• This catalyst was prepared in the same manner as in Example 7, with the exception that the amount of Sn was 1 wt % based on the total weight of the catalyst.
• This catalyst was prepared in the same manner as in Example 7, with the exception that the amount of Sn was 20 wt % based on the total weight of the catalyst.

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